The major product of the following reaction is:
Hydrocarbons · Class 11 · JEE Main Previous Year Question
The major product of the following reaction is:
- a✓
- b
- c
- d
Step 1: Identify the starting material
The starting material is 1,2-dihydronaphthalene (tetralin with one double bond in the ring) treated with in the presence of ethanol ().
Step 2: Bromonium ion formation
When reacts with the alkene in the presence of an alcohol:
- Bromonium ion () forms on the double bond → cyclic bromonium intermediate
- The nucleophile (EtOH, not ) attacks the bromonium ion
- EtOH attacks at the more electrophilic carbon (benzylic position)
- Anti addition → trans product
Step 3: Regiochemistry and stereochemistry
- EtOH attacks at the benzylic carbon (C1 of the ring system, adjacent to aromatic ring) — more electrophilic due to benzylic stabilization
- is incorporated at C2
- Anti addition → trans configuration of OEt and Br
Product = trans-1-ethoxy-2-bromotetralin (trans-2-bromo-1-ethoxytetralin)
Answer: Option (a)
Key Points to Remember:
- In ROH solvent, the alcohol acts as the nucleophile (instead of ) → mixed product
- EtOH attacks the more electrophilic (benzylic) carbon
- Anti addition → trans relationship between OR and Br
- This reaction is used to make bromohydrin ethers
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